Synthesis and fluorescence studies of novel bisarylmethylidene derivatives of 2-methoxy-2-methyl-1,3-dioxan-5-one

Abstract

The first general procedure is described for the synthesis of novel bisarylmethylidenes of 2-methoxy-2-methyl-1,3-dioxan-5-one 1. Thus, several derivatives of 3 are obtained rapidly in high yields by reacting 1 with different aldehydes in the presence of catalytic quantities of pyrrolidine in EtOH at room temperature. Upon completion of the reactions, products are obtained directly by spontaneous precipitation avoiding time consuming and expensive chromatographic separations. All products were characterized by proton and carbon NMR spectroscopy methods, and in one case, the proposed structure was elucidated by X-ray crystallography, confirming the Z stereochemistry for the olefinic C=C bonds. Due to showing different colours in solid and solution states, products were studied for their photophysical properties as well.